One Direction’s Harry Styles may look like he’s 14, but that’s just the number of years between Styles and his now-ex-girlfriend, Caroline Flack. The 18-year-old, whose unruly head of hair may become more famous than Bieber’s swoop, claimed he was simply going through a phase when getting involved with Flack. Following the fallout, Styles was overheard saying that he’s over “older women” at a Brit Awards after party. Aw, Harry. Whatever happened to “age ain’t nothin’ but a number?”

Maybe Styles didn’t tell Flack what makes her beautiful enough.

Flack, a British TV host, says dating the pop star wasn’t easy, either. “Everyone had their opinion on me and Harry,” the 32-year-old told UK entertainment site “The People.” She reportedly couldn’t handle the pressure, and fled to Africa for a month after the two called it quits. Great way to deal with your problems and ditch the spotlight, Flack. Since then, the boy band member has been seen with Mick Jagger’s daughter, Georgia May, who is a mere two years older than the pop singer. For a moment, I thought Styles may be taking the Bieber route (Jelena FTW) but just last week he was holding up a poster of 31-year-old Kim Kardashian with a note saying “Call Me Maybe?” — referring to Carly Rae Jepson’s infectious pop hit. Perhaps that “older women” phase is lasting a tad longer than expected.

Styles isn’t the first guy to be seduced by an older woman, er, a “cougar.” Comedian Nick Cannon, perhaps most well known for his gigs on Nickelodeon, married singer Mariah Carey in 2008 when the two were 27 and 38, respectively. The pair had been dating for only six weeks and now have twins together. Go figure.

Actress Jennifer Aniston flung around with notable soft rocker John Mayer for a while back in 2008. Unlike Cannon, Mayer didn’t want a serious relationship with a woman 10 years older. Well, that’s not entirely true — Mayer never wants a serious relationship with anyone. Just ask Taylor Swift, Jessica Simpson or Minka Kelly.

Though he’s engaged to actress Jessica Biel now, Justin Timberlake dated Cameron Diaz from 2003 to 2007. Diaz, who is 11 years older than Timberlake, was replaced by a younger, sexier starlet — Scarlett Johansson. The affair, sparked on the set of the music video for Timberlake’s 2007 single, “What Goes Around…Comes Around,” didn’t last long.

Be careful, folks. In Cougarville, even solidified relationships can snap in a second. Just ask Ashton and Demi.

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Allison Berger is a Philadelphia-based writer and a pop music columnist for Reverb. Check out more of her writing here.